Sodium Hydroxide → HCID 178462888, compound

HRID 2374495Notes

Reaction equation

HRID 2374495 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[NH:23][C:10]3=[CH:11][C:12]4[C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[N:15]([CH2:18][CH3:19])[C:16]=4[CH:17]=[C:9]3[N:8]=2)=[N:4][NH:5][CH:6]=1.C(N(C(C)C)CC)(C)C.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.[OH-].[Na+]>C1COCC1>[CH2:18]([N:15]1[C:16]2[CH:17]=[C:9]3[N:8]=[C:7]([C:3]4[C:2]([NH:1][C:38](=[O:39])[C:37]5[CH:41]=[CH:42][C:34]([F:33])=[CH:35][CH:36]=5)=[CH:6][NH:5][N:4]=4)[NH:23][C:10]3=[CH:11][C:12]=2[C:13]([CH3:22])([CH3:21])[C:14]1=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178462936HCID 178462936, compound

Product 1

HCID 178462888HCID 178462888, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-amino-1H-pyrazol-3-yl)-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (250 mg, 0.81 mmol), diisopropylethylamine (0.36 ml, 2.01 mmol) in THF (0.8 ml), 4-fluorobenzoyl chloride (114 μL, 0.97 mmol) was slowly added at rt. The mixture was stirred overnight at rt. Aqueous NaOH (2 mL, 1M) was added and the solvent was evaporated. Water (25 ml) was added and the mixture was extracted three times with ethyl acetate (3×25 ml). The combined organic layers were washed with brine, dried and evaporated to afford a residue which precipitated after addition of methanol. The precipitate was suspended in MeOH/CH3CN (1:1, 6 mL) and refluxed for 2 hours in aqueous KOH (0.50 mL, 5M). After evaporation of the solvent and addition of water, a white solid was isolated and dried under high vacuum. The title compound was obtained (77 mg).

Workup

  1. customthe solvent was evaporated
  2. additionWater (25 ml) was added
  3. extractionthe mixture was extracted three times with ethyl acetate (3×25 ml)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. customevaporated
  7. customto afford a residue which
  8. customprecipitated
  9. additionafter addition of methanol
  10. temperaturerefluxed for 2 hours in aqueous KOH (0.50 mL, 5M)
  11. customAfter evaporation of the solvent and addition of water
  12. customa white solid was isolated
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-4ad173f23f244011a5c145de029705b7
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

Loading…